Acetic Anhydride → Alphanitro-6-chloro-3-indoleacrylic acid methylester

HRID 127498

Reaktionsgleichung

Reaktionsgleichung von HRID 127498
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:11][O:12][C:13](=[O:22])[C:14]([N+:19]([O-:21])=[O:20])=[CH:15]OCC.C(OC(=O)C)(=O)C>>[CH3:11][O:12][C:13](=[O:22])[C:14]([N+:19]([O-:21])=[O:20])=[CH:15][C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1

Komponenten

4

Edukt 3

HCID 7918Acetic AnhydrideHCID 871116-ChloroindoleHCID 53395203alpha-Nitro-beta-ethoxyacrylic acid methylester

Produkt 1

HCID 53746644Alphanitro-6-chloro-3-indoleacrylic acid methylesterAusbeute 51 %

Versuchsvorschrift

A 4-1. battery jar was charged with 641 g (4.23 moles) of 6-chloroindole, 926 g (5.3 moles) of crude (ca. 85% pure) alpha-nitro-beta-ethoxy acrylic acid methylester and 475 L g (4.65 moles) of acetic anhydride. The mixture was well stirred at room temperature for 45 hours to give a highly viscous suspension of an orange precipitate. 1.5 l of a mixture of benzene-ether-hexane 1:1:3 was added and the mixture stirred vigorously for 30 minutes. The product was collected by filtration, washed with 1.0 l of the same solvent mixture and dried at room temperature and 16 mmHg to constant weight to afford 600 g (51%) of product as orange crystals, m.p. 159°-160°.

Aufarbeitung

  1. customto give
  2. additiona highly viscous suspension of an orange precipitate
  3. stirringthe mixture stirred vigorously for 30 minutes
  4. filtrationThe product was collected by filtration
  5. washwashed with 1.0 l of the same solvent mixture
  6. customdried at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-cd9b77a451e04e88b7d5f464f6d58049
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256641

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